A Mile in My Shoes is a character driven story of family loyalty, street life, and ultimately love. The story revolves around three adult siblings and their resultant lives following the murder of their mother. Allysa leaves an abusive marriage with an alcoholic husband, and struggles with the dichotomy of reconciliation or raising her son on her own. She goes to live with Charlene, her older and inter-racially married sister. Charlene is entangled in an affair with a man, whom unbeknownst to her is being represented by her divorce lawyer husband. Both sisters are surprised to learn that their brother Hollywood has escaped from a prison in Florida, and is believed to be back in New York City. Hollywood, convicted of a crime that he did not commit but unable to prove it. searches for the one "big score" that will allow him to cling to love, and squirm from the grasp of the criminal life that drew him to hang out on "The Ave."